Episode 3: Dan Shipper

02 Jun Episode 3: Dan Shipper

The Scorecard is Learning

Dan Shipper

Dan is a Wunderkid entrepreneur who has been building web apps since he was a kid. He went to Penn as a Philosophy major and bootstrapped his startup Firefly which he sold the same month as his graduation. So what happens to your internal monologue when you sell your company at a time when most grads are starting their first jobs? There’s the common story that says “When X happens, my life will begin.” But you wouldn’t say “I’ll start exercising once I get promoted to Managing Director?” Dan vulnerably shares deeper insecurities of social rejection, the emotional drain of self talk, and how a relentless drive to improve can be destructive. We riff on writing (how it’s like compound interest and creates serendipity), the dangers of putting off working on yourself, not doing “half a push-up” (when it comes to experimentation), and the lumpy nature of progress. And together we have a good laugh comparing how Dan and I, both nerdy, skinny and insecure teenagers hatched up detailed plans for social acceptance.